Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes

被引：8

作者：

Velasco-Rubio, Alvaro ^{[1
]}

Bernardez, Rodrigo ^{[1
]}

Varela, Jesus A. ^{[1
]}

Saa, Carlos ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biolox & Mat Mol, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 15期

关键词：

FORMAL TOTAL-SYNTHESIS; INTRAMOLECULAR HYDROAMINATION; TERMINAL OLEFINS; ONE-POT; TANDEM; HETEROCYCLES; ANNULATION; ISOCHROMANS; CYCLIZATION; ALLYLATION;

D O I：

10.1021/acs.joc.1c01268

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzofused seven-membered heterocycles such as 1,4-benzo[e]diazepines (1,4-BZDs) and 1,4-benzo[e]oxazepines (1,4-BZOs) were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. The asymmetric hydroamination of (aminomethyl)anilines gave rise to 3-vinyl-1,4-BZDs with excellent enantioselectivities. Orthogonal N-deprotection of 1,4-BZDs allowed an easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptan.

引用

页码：10889 / 10902

页数：14

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